Combinations Comprising a Fungicidal Strain and an Active Compound

ABSTRACT

Fungicidal mixtures, comprising 1) a fungicidal strain (I) selected from a) the  Bacillus substilis  strain with NRRL Accession No. B-21661, and b) the  Bacillus pumilus  strain with NRRL Accession No. B-30087, or a mutant of these strains having all the identifying characteristics of the respective strain, or a metabolite produced by the respective strain that exhibits activity against plant pathogenic fungi, and 2) at least one chemical compound (II), selected from the active compound groups A) to F): A) azoles; B) strobilurins; C) carboxamides; D) heterocyclic compounds; E) carbamates; F) other fungicides; in a synergistically effective amount, methods for controlling harmful fungi using compositions of components 1) and 2), the use of a component 1) with a component 2) for preparing such compositions, and also fungicidal agents and seed comprising such compositions.

The present invention relates to fungicidal compositions for controlling phytopathogenic harmful fungi comprising, as active components,

-   1) a fungicidal strain (I) selected from     -   a) the Bacillus substilis strain with NRRL Accession No.         B-21661, and     -   b) the Bacillus pumilus strain with NRRL Accession No. B-30087,         or a mutant of these strains having all the identifying         characteristics of the respective strain, or a metabolite         produced by the respective strain that exhibits activity against         plant pathogenic fungi;         and -   2) at least one chemical compound (II), selected from the active     compound groups A) to F):     -   A) azoles selected from the group consisting of azaconazole,         diniconazole-M, oxpoconazol, paclobutrazol, uniconazol,         1-(4-chloro-phenyl)-2-([1,2,4]triazol-1-yl)-cycloheptanol and         imazalil-sulfphate;     -   B) strobilurins selected from the group consisting of         2-(2-(6-(3-chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methylacetamide         and         3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropanecarboximidoylsulfanylmethyl)-phenyl)-acrylic         acid methyl ester;     -   C) carboxamides selected from the group consisting of benalaxyl,         benalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxamide,         2-chloro-N-(1,1,3-trimethyl-indan-4-yl)-nicotinamide,         N-(2-(1,3-dimethylbutyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide,         N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,         N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,         N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,         N-(trans-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,         fluopyram,         N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide,         oxytetracyclin, silthiofam,         N-(6-methoxypyridin-3-yl)cyclopropanecarboxylic acid amide,         penthiopyrad, isopyrazam and a 1-methyl-pyrazol-4-ylcarboxamide         of the formula III

-   -   -   in which the substituents are as defined below:         -   X is hydrogen or fluorine;         -   R¹ is C₁-C₄-alkyl or C₁-C₄-haloalkyl;         -   R² is hydrogen or halogen;         -   R³, R⁴ and R⁵ independently of one another are hydrogen,             cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,             C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or             C₁-C₄-haloalkyl;

    -   D) heterocyclic compounds selected from the group consisting of         5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine,         2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine,         3,4,5-trichloro-pyridine-2,6-dicarbonitrile,         N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4-dichloronicotinamide,         N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4-dichloronicotinamide,         diflumetorim, nitrapyrin, dodemorph-acetate, fluoroimid,         blasticidin-S, chinomethionat, debacarb, oxolinic acid,         piperalin and an azolopyrimidin-7-ylamine of the formula IV

-   -   -   in which the substituents have the following meanings:         -   E¹ is C₃-C₁₂-alkyl, C₂-C₁₂-alkenyl, C₅-C₁₂-alkoxyalkyl,             C₃-C₆-cycloalkyl, phenyl or phenyl-C₁-C₄-alkyl;         -   E² is C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, C₁-C₄-haloalkyl or             C₁-C₄-alkoxy-C₁-C₄-alkyl;         -   where the aliphatic chains in E¹ and/or E² may be             substituted by one to four identical or different groups             R^(a):         -   R^(a) is halogen, cyano, hydroxyl, mercapto,             C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,             C₁-C₆-alkoxy, alkylthio, C₁-C₆-alkoxy-C₁-C₆-alkyl or             NR^(A)R^(B);         -   R^(A), R^(B) independently of one another are hydrogen or             C₁-C₆-alkyl;         -   where the cyclic groups in E¹ and/or R^(a) may be             substituted by one to four groups R^(b):         -   R^(b) is halogen, cyano, hydroxyl, mercapto, nitro,             NR^(A)R^(B), C₁-C₁₀-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,             C₂-C₆-alkynyl or C₁-C₆-alkoxy;         -   E³ is hydrogen, halogen, cyano, NR^(A)R^(B), hydroxyl,             mercapto, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,             C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₈-cycloalkoxy,             C₃-C₈-cycloalkylthio, carboxyl, formyl,             C₁-C₁₀-alkylcarbonyl, C₁-C₁₀-alkoxycarbonyl,             C₂-C₁₀-alkenyloxycarbonyl, C₂-C₁₀-alkynyloxycarbonyl,             phenyl, phenoxy, phenylthio, benzyloxy, benzylthio or             C₁-C₆-alkyl-S(O)_(m)—;         -   m is 0, 1 or 2;         -   A is CH or N;

    -   E) carbamates selected from the group consisting of         methasulphocarb and propamocarb hydrochlorid;

    -   F) other fungicides selected from the group consisting of         metrafenone, dodine free base, guazatine-acetate,         iminoctadine-triacetate, iminoctadine-tris(albesilate),         kasugamycin-hydrochlorid-hydrat, dichlorophen, pentachlorophenol         and its salts,         N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfon-amide,         dicloran, nitrothal-isopropyl, tecnazen, biphenyl, bronopol,         diphenylamine, mildiomycin, oxin-copper, prohexadione calcium,         N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl         acetamide,         N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl         formamidine,         N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl         formamidine,         N′-(2-methyl-5-trifluormethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl         formamidine and         N′-(5-difluormethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl         formamidine;

    -   in a synergistically effective amount.

Moreover, the invention relates to a method for controlling harmful fungi using a composition of components 1) and 2), to the use of a component 1) with a component 2) for preparing such compositions, and also to agents and seed comprising such compositions.

The strains (I), their mutants and the metabolites produced by the strains that exhibit activity against plant pathogenic fungi, referred to above as component 1), their preparation and their action against harmful fungi are known from WO 98/50422, WO 00/29426 and WO 00/58442, therein also referred to as AQ713 (QST713) and QST2808.

Isolates of bacteria of species Bacillus subtilis and Bacillus pumilus which are effective in inhibiting the growth of fungi of species botrytis cinerea and/or Alternaria brassicicola and a method of obtaining those isolates are also known from WO 93/18654.

Example 13 of WO 98/50422 already discloses that synergistic activity is obtained by the combined treatment of component 1) a) and azoxystrobin.

NRRL is the abbreviation for the Agricultural Research Service Culture Collection, an international depositary authority for the purposes of deposing microorganism strains under the BUDAPEST TREATY ON THE INTERNATIONAL RECOGNITION OF THE DEPOSIT OF MICROORGANISMS FOR THE PURPOSES OF PATENT PROCEDURE, having the address National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, Peoria, Ill. 61604, USA.

Suitable formulations of the Bacillus subtilis strain 1) a) are commercially available under the tradenames RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc., USA.

Suitable formulations of the Bacillus pumilus strain 1) b) are commercially available under the tradenames SONATA® and BALLAD® Plus from AgraQuest, Inc., USA.

However, the known strains (I), their mutants and the metabolites produced by the strains are, in particular at low application rates, not entirely satisfactory.

The active compounds (II) mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.

N-(2-bicycloprop-2-yl-phenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide is known from WO 03/074491 and can be prepared in the manner described therein. The fungicidal activity of said compound against various harmful fungi is known from WO 2006/015866.

Isopyrazam is known from WO 04/035589 and can be prepared in the manner described therein or as described in WO 2007/068417.

The 1-methyl-pyrazol-4-ylcarboxanilides of formula (III) are known from the literature (cf., for example, EP-A 545 099, EP-A 589 301, WO 99/09013, WO 2003/70705 and WO 2006/087343), or they can be prepared in the manner described therein.

The azolopyrimidin-7-ylamines IV, their preparation and their action against harmful fungi are known from the literature (EP-A 71 792; EP-A 141 317; WO 03/009687; WO 05/087771; WO 05/087772; WO 05/087773; WO 2005/087772; WO 2006/087325; WO 2006/092428).

Metrafenone, 3′-bromo-2,3,4,6′-tetramethoxy-2′,6-dimethylbenzophenone, is known from U.S. Pat. No. 5,945,567.

It was an object of the present invention, with a view to reducing the application rates and broadening the activity spectrum of the strains (I) and compounds (II), to provide compositions which, at a reduced total amount of active compounds applied, have improved activity against harmful fungi, in particular for certain indications.

We have accordingly found that this object is achieved by the compositions, of components 1) and 2), defined at the outset. Moreover, we have found that simultaneous, that is joint or separate, application of components 1) and 2) or successive application of the components 1) and 2) allows better control of harmful fungi than is possible with the strains, their mutants and the metabolites produced by the strains on the one hand and with the individual compounds (II) on the other hand, alone (synergistic mixtures).

By simultaneous, that is joint or separate, application of components 1) and 2), the fungicidal activity is increased in a superadditive manner.

Component 1) embraces not only the isolated, pure cultures of the Bacillus substilis strain and the Bacillus pumilus strain, but also their suspensions in a whole broth culture or as a metabolite-containing supernatant or a purified metabolite obtained from a whole broth culture of the strain.

“Whole broth culture” refers to a liquid culture containing both cells and media.

“Supernatant” refers to the liquid broth remaining when cells grown in broth are removed by centrifugation, filtration, sedimentation, or other means well known in the art.

The term “metabolite” refers to any compound, substance or byproduct of a fermentation or a microorganism that has fungicidal activity.

Preferred component 1) is a fungicidal strain 1) a), the Bacillus substilis strain with NRRL Accession No. B-21661, a mutant thereof having all the identifying characteristics of the strain, or a metabolite produced by the strain that exhibits activity against plant pathogenic fungi.

Many of the active compounds II can be present in different crystal modifications, which may differ in biological activity. They also form part of component 2).

Preference is given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of A) azoles.

Preference is also given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of B) strobilurins.

Preference is given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of C) carboxamides.

Among the group of C) carboxamides, penthiopyrad, N-(2-(1,3-dimethylbutyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(trans-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide and the 1-methyl-pyrazol-4-ylcarboxanilides of the formula III are preferred.

In the formula III, halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;

C₁-C₄-alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, preferably methyl or ethyl;

C₁-C₄-haloalkyl is a partially or fully halogenated C₁-C₄-alkyl radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, heptafluoropropyl or nonafluorobutyl, in particular halomethyl, with particular preference CH₂—Cl, CH(Cl)₂, CH₂—F, CHF₂, CF₃, CHFCl, CF₂Cl or CF(Cl)₂, in particular CHF₂ or CF₃;

C₁-C₄-alkoxy is OCH₃, OC₂H₅, OCH₂—C₂H₅, OCH(CH₃)₂, n-butoxy, OCH(CH₃)—C₂H₅, OCH₂—CH(CH₃)₂ or OC(CH₃)₃, preferably OCH₃ or OC₂H₅;

C₁-C₄-haloalkoxy is a partially or fully halogenated C₁-C₄-alkoxy radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, heptafluoropropoxy or nonafluorobutoxy, in particular halomethoxy, particularly preferably OCH₂—Cl, OCH(Cl)₂, OCH₂—F, OCH(F)₂, OCF₃, OCHFCl, OCF₂Cl or OCF(Cl)₂;

C₁-C₄-alkylthio is SCH₃, SC₂H₅, SCH₂—C₂H₅, SCH(CH₃)₂, n-butylthio, SCH(CH₃)—C₂H₅, SCH₂—CH(CH₃)₂ or SC(CH₃)₃, preferably SCH₃ or SC₂H₅.

C₁-C₄-haloalkylthio is a partially or fully halogenated C₁-C₄-alkylthio radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio, heptafluoropropylthio or nonafluorobutylthio, in particular halomethylthio, particularly preferably SCF₃;

Preferred 1-methylpyrazol-4-ylcarboxanilides III are, on the one hand, those in which X is hydrogen.

On the other hand, preferred compounds III are those in which X is fluorine.

For the mixtures according to the invention, preference is given to compounds of the formula III in which R¹ is methyl or halomethyl, in particular CH₃, CHF₂, CH₂F, CF₃, CHFCl or CF₂Cl.

Preference is furthermore given to compounds III in which R² is hydrogen, fluorine or chlorine, in particular hydrogen.

Preference is furthermore given to those compounds III in which R³ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkylthio, preferably halogen, methyl, halomethyl, methoxy, halomethoxy or methylthio, in particular F, Cl, CH₃, CF₃, OCH₃, OCHF₂, OCF₃ or SCH₃, particularly preferably fluorine.

Moreover, preference is given to those compounds III in which R⁴ is halogen, in particular fluorine.

Preference is furthermore given to those compounds III in which R⁵ is halogen, in particular fluorine.

Among those 1-methylpyrazol-4-ylcarboxanilides III where X is hydrogen, particular preference is given to N-(2′-fluoro-4′-chloro-5′-methoxybiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′-fluoro-4′-chloro-5′-methylbiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′,4′,5′-trifluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′-fluoro-4′-chloro-5′-methoxybiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′,3′,4′-trifluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′-fluoro-4′-chloro-5′-methylbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′,4′,5′-trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-fluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-chlorodifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′,3′,4′-trifluorobiphenyl-2-yl)-3-fluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2′,4′,5′-trifluorobiphenyl-2-yl)-3-fluoro-methyl-1-methyl-1H-pyrazole-4-carboxamide, N-(4′-trifluoromethylthio-biphenyl-2-yl)-3-difluoro-methyl-1-methyl-1H-pyrazole-4-carboxamide and N-(4′-trifluoromethylthio-biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide.

Among those 1-methylpyrazol-4-ylcarboxanilides I where X is fluorine, particular preference is given to N-(3′,4′-dichloro-3-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-dichloro-3-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-difluoro-3-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-difluoro-3-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′-chloro-4′-fluoro-3-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-difluoro-4-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-difluoro-4-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′-chloro-4′-fluoro-4-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-difluoro-5-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-difluoro-5-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-1,3-dimethyl-1H-pyrazole-4-carboxamide, N-(3′-chloro-4′-fluoro-5-fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N-(4′-fluoro-4-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(4′-fluoro-5-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(4′-chloro-5-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(4′-methyl-5-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N-(4′-fluoro-5-fluorobiphenyl-2-yl)-1,3-dimethyl-1H-pyrazole-4-carboxamide, N-(4′-chloro-5-fluorobiphenyl-2-yl)-1,3-dimethyl-1H-pyrazole-4-carboxamide, N-(4′-methyl-5-fluorobiphenyl-2-yl)-1,3-dimethyl-1H-pyrazole-4-carboxamide, N-(4′-fluoro-6-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide and N-(4′-chloro-6-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide.

Preference is furthermore also given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of D) heterocyclic compounds.

Among the D) heterocyclic compounds, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine and the azolopyrimidin-7-ylamines of the formula IV are preferred.

In the formula IV, halogen is fluorine, chlorine, bromine or iodine.

alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 1 to 6, 1 to 10, 1 to 12 or 3 to 12 carbon atoms, for example C₁-C₆-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

-   -   haloalkyl: straight-chain or branched alkyl radicals having 1 to         4, 1 to 6 or 1 to 10 carbon atoms (as mentioned above), where         some or all of the hydrogen atoms in these radicals may be         replaced by halogen atoms as mentioned above: in particular         C₁-C₂-haloalkyl such as chloromethyl, bromomethyl,         dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl,         trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,         chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,         1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,         2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, pentafluoroethyl or         1,1,1-trifluoroprop-2-yl;     -   alkenyl: unsaturated straight-chain or branched hydrocarbon         radicals having 2 to 6, 2 to 10 or 2 to 12 carbon atoms and one         or two double bonds in any position, for example C₂-C₆-alkenyl,         such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl,         1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,         2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,         1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,         1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,         1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,         1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,         1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,         1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,         1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,         1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,         4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,         3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,         2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,         1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,         4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,         1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl,         1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,         1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl,         1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl,         2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,         2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl,         3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl,         1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl,         2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,         1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl or         1-ethyl-2-methyl-2-propenyl;

alkynyl: straight-chain or branched hydrocarbon radicals having 2 to 6 or 2 to 10 carbon atoms and one or two triple bonds in any position, for example C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl or 1-ethyl-1-methyl-2-propynyl;

cycloalkyl: mono- or bicyclic saturated hydrocarbon radicals having 3 to 6 or 3 to 8 carbon ring members, for example C₃-C₈-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;

cycloalkoxy: mono- or bicyclic saturated hydrocarbon radicals which are attached via an oxygen atom (—O—);

cycloalkylthio: mono- or bicyclic, saturated hydrocarbon radicals which are attached via a sulfur atom (—S—);

alkylthio: saturated, straight-chain or branched hydrocarbon radicals which are attached via a sulfur atom (—S—);

alkylcarbonyl: straight-chain or branched alkyl radicals which have 1 to 10 carbon atoms and are attached via a carbonyl group (—CO—);

alkoxy: straight-chain or branched alkyl radicals which are attached via an oxygen atom (—O—);

alkoxyalkyl: straight-chain or branched alkoxy radicals which are attached to an alkyl radical;

haloalkoxy: straight-chain or branched alkoxy radicals, where some or all of the hydrogen atoms in these radicals may be replaced by halogen;

alkoxycarbonyl: alkoxy radicals which have 1 to 10 carbon atoms and are attached via a carbonyl group (—CO—);

alkenyloxycarbonyl: alkenyl radicals which are attached via an oxygen atom (—O—) to a carbonyl group (—CO—);

alkynyloxycarbonyl: alkynyl radicals which are attached via an oxygen atom (—O—) to a carbonyl group (—CO—);

-   -   phenylalkyl: a phenyl group which is attached via saturated,         straight-chain or branched alkyl radicals.

Preferred azolopyrimidin-7-ylamines IV are those compounds in which E¹ is straight-chain or branched C₃-C₁₂-alkyl or phenyl which may be substituted by one to three halogen or C₁-C₄-alkyl groups.

In one embodiment of the compounds IV, the aliphatic chains in E¹ and E² or in E¹ or E² are not substituted by R^(a).

A preferred embodiment relates to compounds IV in which E¹ is straight-chain or branched C₅-C₁₀-alkyl, in particular ethyl, 3,5,5-trimethylhexyl, n-heptyl, n-octyl, n-nonyl or n-decyl.

A further embodiment relates to compounds IV in which E¹ is phenyl which is unsubstituted or substituted by one to four radicals R^(b).

Preferred compounds IV are those in which E¹ is a substituted phenyl group which corresponds to a group Ar

in which L¹ to L³ are halogen, cyano, hydroxyl, mercapto, nitro, NR^(A)R^(B), C₁-C₁₀-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₁-C₆-alkoxy; r and q independently of one another may be 0 or 1 sein, where NR^(A)R^(B) is as defined in formula IV and #denotes the bond to the azolopyrimidine skeleton.

In a further embodiment of the compounds IV, L is halogen, cyano, hydroxyl, mercapto, nitro, NR^(A)R^(B), C₁-C₆-alkyl, halomethyl and C₁-C₂-alkoxy, preferably halogen, cyano, C₁-C₆-alkyl, halomethyl or C₁-C₂-alkoxy.

In a further embodiment of the compounds IV, q is 0 or L² is one of the groups mentioned above and q is 1.

In a further embodiment of the compounds IV, r is 0 or L³ is halogen, cyano, hydroxyl, mercapto, nitro, NR^(A)R^(B), C₁-C₆-alkyl, halomethyl or C₁-C₂-alkoxy and r is 1. Preferably, r is zero.

Preference is given to compounds IV in which E² is straight-chain or branched C₁-C₁₂-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl or C₁-C₄-haloalkyl.

In a particularly preferred embodiment of the compounds IV, E² is methyl, ethyl, n-propyl, n-octyl, trifluoromethyl or methoxymethyl, in particular methyl, ethyl, trifluoromethyl or methoxymethyl.

Preference is furthermore given to compounds IV in which E³ is hydrogen.

In a further embodiment of the compounds IV, E³ is amino.

One embodiment of the compounds IV relates to those in which A is N. These compounds correspond to formula IVa in which the variables are as defined for formula IV:

Another embodiment of the compounds of the formula IV relates to those in which A is CH. These compounds correspond to formula IVb in which the variables are as defined for formula IV:

In a further embodiment of preferred compounds IV, the sum of the carbon atoms in the carbon radicals of E¹ and E² is not more than 12.

TABLE 1 No. Compound IV.1 6-(3,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.2 6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.3 5-methyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.4 5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.5 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-2,7-diamine IV.6 6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.7 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.8 5-ethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.9 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.10 5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.11 6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine IV.12 5-trifluoromethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine

Preference is furthermore also given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of E) carbamates.

Preference is furthermore also given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of F) other fungicides.

Preference is also given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of F) other fungicides selected from the group consisting of metrafenone, dodine free base, guazatine-acetate, iminoctadine-triacetate, iminoctadine-tris(albesilate), kasugamycin-hydrochlorid-hydrat, dichlorophen, pentachlorophenol and its salts, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfon-amide, dicloran, nitrothal-isopropyl, tecnazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxin-copper and prohexadione calcium, in particular metrafenone, dodine free base, guazatine-acetate, iminoctadine-triacetate, iminoctadine-tris(albesilate), nitrothal-isopropyl, mildiomycin, oxin-copper and prohexadione calcium. Very particularly preferred is metrafenone.

Particular preference is given to compositions of a compound 1) with a component 2) consisting of at least one active compound (II) selected from groups C), D) and F), whereas each of C), D) and F) may consist of all members or the preferred embodiments.

Preference is also given to three-component compositions comprising a component 1), wherein component 2) consists of two of the active compounds (II) mentioned above.

Preference is also given to three-component compositions comprising, in addition to component 1) and component 2) consisting of one active compound (II) mentioned above, a further fungicidally active compound V selected from active compound groups G) to M):

-   G) azoles selected from the group consisting of bitertanol,     bromuconazole, cyproconazole, difenoconazole, diniconazole,     enilconazole, epoxiconazole, fluquinconazole, fenbuconazole,     flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole,     metconazole, myclobutanil, penconazole, propiconazole,     prothioconazole, simeconazole, triadimefon, triadimenol,     tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate,     imazalil, triflumizole, cyazofamid, benomyl, carbendazim,     thiabendazole, fuberidazole, ethaboxam, etridiazole and hymexazole; -   H) strobilurins selected from the group consisting of azoxystrobin,     dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl,     methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,     trifloxystrobin, enestroburin, methyl     (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate,     methyl     (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate     and methyl     2-(ortho-(2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate; -   J) carboxamides selected from the group consisting of carboxin,     boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl,     mefenoxam, ofurace, oxadixyl, oxycarboxin, thifluzamide, tiadinil,     3,4-dichloro-N-(2-cyanophenyl)iso-thiazole-5-carboxamide,     penthiopyrad, dimethomorph, flumorph, flumetover, fluopicolide     (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid,     N-(2-(4-[3-(4-chlorophenyl)     prop-2-ynyloxy]-3-ethoxyphenyl)ethyl)-2-methanesulfonylamino-3-methylbutyramide,     N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-ethanesulfonylamino-3-methylbutyramide,     methyl     3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propionate,     N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carbox-amide,     N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide,     N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methyl-thiazole-5-carboxamide,     N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide     and N-(2-cyanophenyl)-3,4-dichloroisothiazole-5-carboxamide; -   K) heterocyclic compounds selected from the group consisting of     fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone,     mepanipyrim, nuarimol, pyrimethanil, triforine, fenpiclonil,     fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph,     fenpropidin, iprodione, procymidone, vinclozolin, famoxadone,     fenamidone, octhilinone, probenazole,     5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine,     anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole,     2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-S-methyl,     captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen and     N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide; -   L) carbamates selected from the group consisting of mancozeb, maneb,     metam, metiram, ferbam, propineb, thiram, zineb, ziram,     diethofencarb, iprovalicarb, flubenthiavalicarb, propamocarb,     4-fluorophenyl     N-(1-(1-(4-cyanophenyl)ethanesulfonyl)but-2-yl)carbamate, methyl     3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propanoate     and carbamate oxime ethers of the formula VI

-    in which Z is N or CH; -   M) other fungicides selected from the group consisting of guanidine,     dodine, iminoctadine, guazatine,     -   antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A,     -   nitrophenyl derivatives: binapacryl, dinocap, dinobuton,     -   sulfur-containing heterocyclyl compounds: dithianon,         isoprothiolane,     -   organometallic compounds: fentin salts such as fentin acetate,     -   organophosphorus compounds: edifenphos, iprobenfos, fosetyl,         fosetyl-aluminum, phosphorous acid and its salts, pyrazophos,         tolclofos-methyl,     -   organochlorine compounds: chlorothalonil, dichlofluanid,         flusulfamide, hexachlorbenzene, phthalide, pencycuron,         quintozene, thiophanate-methyl, tolylfluanid,     -   inorganic active compounds: Bordeaux mixture, copper acetate,         copper hydroxide, copper oxychloride, basic copper sulfate,         sulfur,     -   others: cyflufenamid, cymoxanil, dimethirimol, ethirimol,         furalaxyl and spiroxamine.

The active compounds V mentioned above, their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.

Preference is given to three-component compositions of components 1) and 2) with an active compound V selected from the group of the azoles G).

Preference is also given to three-component compositions of components 1) and 2) with an active compound V selected from the group of the strobilurins H).

Preference is given to three-component compositions of components 1) and 2) with an active compound V selected from the group of the carboxamides J).

Preference is furthermore also given to three-component compositions of components 1) and 2) with an active compound V selected from the group of the heterocyclic compounds K).

Preference is furthermore also given to three-component compositions of components 1) and 2) with an active compound V selected from the group of the carbamates L).

Preference is furthermore also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the other fungicides M).

Preference is furthermore also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the azoles G) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam.

Particular preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the azoles G) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl and carbendazim.

Very particular preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the azoles G) selected from the group consisting of epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim.

Preference is also given to three-component compositions of components 1) and 2) with at least one active compound selected from the group of the strobilurins H) selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.

Particular preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the strobilurins H) selected from the group consisting of kresoxim-methyl, orysastrobin and pyraclostrobin.

Very particular preference is also given to three-component compositions of components 1) and 2) with pyraclostrobin.

Preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the carboxamides J) selected from the group consisting of fenhexamid, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamid), zoxamide, carpropamid and mandipropamid.

Particular preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the carboxamides J) selected from the group consisting of fenhexamid, metalaxyl, mefenoxam, ofurace, dimethomorph, zoxamide and carpropamid.

Preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the heterocyclic compounds J) selected from the group consisting of fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforine, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen, in particular fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforine, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen.

Particular preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the heterocyclic compounds K) selected from the group consisting of pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozolin and quinoxyfen, in particular pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozolin and quinoxyfen.

Preference is also given to three-component compositions of components 1) and 2) with at least one active compound selected from the group of the carbamates L) selected from the group consisting of mancozeb, metiram, propineb, thiram, iprovalicarb, flubenthiavalicarb and propamocarb.

Particular preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the carbamates L) selected from the group consisting of mancozeb and metiram.

Preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the other fungicides M) selected from the group consisting of dithianon, fentin salts, such as fentin acetate, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, chlorothalonil, dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, cymoxanil and spiroxamine.

Particular preference is also given to three-component compositions of components 1) and 2) with an active compound selected from the group of the other fungicides M) selected from the group consisting of phosphorous acid and its salts and chlorothalonil.

Preference is also given to four-component compositions of components 1) and 2) with two further active compounds selected from compounds II and V mentioned above.

Preferred active compound combinations are listed in tables 2 to 7 below:

TABLE 2 Active compound combinations of a component 1) and a component 2), conprising a compound II selected from group A): Mixture Component 1) Component 2) No. A.1 RHAPSODY ® azaconazole No. A.2 SERENADE ® MAX azaconazole No. A.3 SERENADE ® ASO azaconazole No. A.4 SONATA ® azaconazole No. A.5 BALLAD ® Plus azaconazole No. A.6 RHAPSODY ® diniconazole-M No. A.7 SERENADE ® MAX diniconazole-M No. A.8 SERENADE ® ASO diniconazole-M No. A.9 SONATA ® diniconazole-M No. A.10 BALLAD ® Plus diniconazole-M No. A.11 RHAPSODY ® oxpoconazol No. A.12 SERENADE ® MAX oxpoconazol No. A.13 SERENADE ® ASO oxpoconazol No. A.14 SONATA ® oxpoconazol No. A.15 BALLAD ® Plus oxpoconazol No. A.16 RHAPSODY ® paclobutrazol No. A.17 SERENADE ® MAX paclobutrazol No. A.18 SERENADE ® ASO paclobutrazol No. A.19 SONATA ® paclobutrazol No. A.20 BALLAD ® Plus paclobutrazol No. A.21 RHAPSODY ® uniconazol No. A.22 SERENADE ® MAX uniconazol No. A.23 SERENADE ® ASO uniconazol No. A.24 SONATA ® uniconazol No. A.25 BALLAD ® Plus uniconazol No. A.26 RHAPSODY ® 1-(4-chloro-phenyl)-2- ([1,2,4]triazol-1-yl)- cycloheptanol No. A.27 SERENADE ® MAX 1-(4-chloro-phenyl)-2- ([1,2,4]triazol-1-yl)- cycloheptanol No. A.28 SERENADE ® ASO 1-(4-chloro-phenyl)-2- ([1,2,4]triazol-1-yl)- cycloheptanol No. A.29 SONATA ® 1-(4-chloro-phenyl)-2- ([1,2,4]triazol-1-yl)- cycloheptanol No. A.30 BALLAD ® Plus 1-(4-chloro-phenyl)-2- ([1,2,4]triazol-1-yl)- cycloheptanol No. A.31 RHAPSODY ® imazalil-sulfphate No. A.32 SERENADE ® MAX imazalil-sulfphate No. A.33 SERENADE ® ASO imazalil-sulfphate No. A.34 SONATA ® imazalil-sulfphate No. A.35 BALLAD ® Plus imazalil-sulfphate

TABLE 3 Active compound combinations of a component 1) and a component 2), conprising a compound II selected from group B): Mixture Component 1) Component 2) No. B.1 RHAPSODY ® 2-(2-(6-(3-chloro-2-methyl-phenoxy)-5-fluoro-pyrimidin-4- yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide No. B.2 SERENADE ® MAX 2-(2-(6-(3-chloro-2-methyl-phenoxy)-5-fluoro-pyrimidin-4- yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide No. B.2 SERENADE ® ASO 2-(2-(6-(3-chloro-2-methyl-phenoxy)-5-fluoro-pyrimidin-4- yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide No. B.1 SONATA ® 2-(2-(6-(3-chloro-2-methyl-phenoxy)-5-fluoro-pyrimidin-4- yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide No. B.2 BALLAD ® Plus 2-(2-(6-(3-chloro-2-methyl-phenoxy)-5-fluoro-pyrimidin-4- yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide No. B.3 RHAPSODY ® 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane- carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester No. B.4 SERENADE ® MAX 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane- carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester No. B.3 SERENADE ® ASO 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane- carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester No. B.3 SONATA ® 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane- carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester No. B.4 BALLAD ® Plus 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane- carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester

TABLE 4 Active compound combinations of a component 1) and a component 2), conprising a compound II selected from group C): Mixture Component 1) Component 2) No. C.1 RHAPSODY ® benalaxyl-M No. C.2 SERENADE ® MAX benalaxyl-M No. C.3 SERENADE ® ASO benalaxyl-M No. C.4 SONATA ® benalaxyl-M No. C.5 BALLAD ® Plus benalaxyl-M No. C.6 RHAPSODY ® 2-amino-4-methyl-thiazole-5-carboxanilide No. C.7 SERENADE ® MAX 2-amino-4-methyl-thiazole-5-carboxanilide No. C.8 SERENADE ® ASO 2-amino-4-methyl-thiazole-5-carboxanilide No. C.9 SONATA ® 2-amino-4-methyl-thiazole-5-carboxanilide No. C.10 BALLAD ® Plus 2-amino-4-methyl-thiazole-5-carboxanilide No. C.11 RHAPSODY ® 2-chloro-N-(1,1,3-trimethyl-indan-4-yl)-nicotinamide No. C.12 SERENADE ® MAX 2-chloro-N-(1,1,3-trimethyl-indan-4-yl)-nicotinamide No. C.13 SERENADE ® ASO 2-chloro-N-(1,1,3-trimethyl-indan-4-yl)-nicotinamide No. C.14 SONATA ® 2-chloro-N-(1,1,3-trimethyl-indan-4-yl)-nicotinamide No. C.15 BALLAD ® Plus 2-chloro-N-(1,1,3-trimethyl-indan-4-yl)-nicotinamide No. C.16 RHAPSODY ® N-(2-(1,3-dimethylbutyl)-phenyl)-1,3-dimethyl-5- fluoro-1H-pyrazole-4-carboxamide No. C.17 SERENADE ® MAX N-(2-(1,3-dimethylbutyl)-phenyl)-1,3-dimethyl-5- fluoro-1H-pyrazole-4-carboxamide No. C.18 SERENADE ® ASO N-(2-(1,3-dimethylbutyl)-phenyl)-1,3-dimethyl-5- fluoro-1H-pyrazole-4-carboxamide No. C.19 SONATA ® N-(2-(1,3-dimethylbutyl)-phenyl)-1,3-dimethyl-5- fluoro-1H-pyrazole-4-carboxamide No. C.20 BALLAD ® Plus N-(2-(1,3-dimethylbutyl)-phenyl)-1,3-dimethyl-5- fluoro-1H-pyrazole-4-carboxamide No. C.21 RHAPSODY ® N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.22 SERENADE ® MAX N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.23 SERENADE ® ASO N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.24 SONATA ® N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.25 BALLAD ® Plus N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.26 RHAPSODY ® N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.27 SERENADE ® MAX N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.28 SERENADE ® ASO N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.29 SONATA ® N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.30 BALLAD ® Plus N-(4′-chloro-3′,5-difluoro-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.31 RHAPSODY ® N-(3′,4′-dichloro-5-fluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.32 SERENADE ® MAX N-(3′,4′-dichloro-5-fluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.33 SERENADE ® ASO N-(3′,4′-dichloro-5-fluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.34 SONATA ® N-(3′,4′-dichloro-5-fluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.35 BALLAD ® Plus N-(3′,4′-dichloro-5-fluoro-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.36 RHAPSODY ® N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.37 SERENADE ® MAX N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.38 SERENADE ® ASO N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.39 SONATA ® N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.40 BALLAD ® Plus N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.41 RHAPSODY ® N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.42 SERENADE ® MAX N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.43 SERENADE ® ASO N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.44 SONATA ® N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.45 BALLAD ® Plus N-(3′,5-difluoro-4′-methyl-biphenyl-2-yl)-3- trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.46 RHAPSODY ® N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1- methyl-1H-pyrazole-4-carboxamide No. C.47 SERENADE ® MAX N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1- methyl-1H-pyrazole-4-carboxamide No. C.48 SERENADE ® ASO N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1- methyl-1H-pyrazole-4-carboxamide No. C.49 SONATA ® N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1- methyl-1H-pyrazole-4-carboxamide No. C.50 BALLAD ® Plus N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1- methyl-1H-pyrazole-4-carboxamide No. C.51 RHAPSODY ® N-(trans-2-bicyclopropyl-2-yl-phenyl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.52 SERENADE ® MAX N-(trans-2-bicyclopropyl-2-yl-phenyl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.53 SERENADE ® ASO N-(trans-2-bicyclopropyl-2-yl-phenyl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.54 SONATA ® N-(trans-2-bicyclopropyl-2-yl-phenyl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.55 BALLAD ® Plus N-(trans-2-bicyclopropyl-2-yl-phenyl)-3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide No. C.56 RHAPSODY ® fluopyram No. C.57 SERENADE ® MAX fluopyram No. C.58 SERENADE ® ASO fluopyram No. C.59 SONATA ® fluopyram No. C.60 BALLAD ® Plus fluopyram No. C.61 RHAPSODY ® N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)-3-formylamino- 2-hydroxy-benzamide No. C.62 SERENADE ® MAX N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)-3-formylamino- 2-hydroxy-benzamide No. C.63 SERENADE ® ASO N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)-3-formylamino- 2-hydroxy-benzamide No. C.64 SONATA ® N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)-3-formylamino- 2-hydroxy-benzamide No. C.65 BALLAD ® Plus N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)-3-formylamino- 2-hydroxy-benzamide No. C.66 RHAPSODY ® oxytetracyclin No. C.67 SERENADE ® MAX oxytetracyclin No. C.68 SERENADE ® ASO oxytetracyclin No. C.69 SONATA ® oxytetracyclin No. C.70 BALLAD ® Plus oxytetracyclin No. C.71 RHAPSODY ® silthiofam No. C.72 SERENADE ® MAX silthiofam No. C.73 SERENADE ® ASO silthiofam No. C.74 SONATA ® silthiofam No. C.75 BALLAD ® Plus silthiofam No. C.76 RHAPSODY ® N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxamide No. C.77 SERENADE ® MAX N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxamide No. C.78 SERENADE ® ASO N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxamide No. C.79 SONATA ® N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxamide No. C.80 BALLAD ® Plus N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxamide No. C.81 RHAPSODY ® N-(2′-fluoro-4′-chloro-5′-methylbiphenyl-2-yl)-1- methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide No. C.82 SERENADE ® MAX N-(2′-fluoro-4′-chloro-5′-methylbiphenyl-2-yl)-1- methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide No. C.83 SERENADE ® ASO N-(2′-fluoro-4′-chloro-5′-methylbiphenyl-2-yl)-1- methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide No. C.84 SONATA ® N-(2′-fluoro-4′-chloro-5′-methylbiphenyl-2-yl)-1- methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide No. C.85 BALLAD ® Plus N-(2′-fluoro-4′-chloro-5′-methylbiphenyl-2-yl)-1- methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide No. C.86 RHAPSODY ® N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- trifluoromethyl-1H-pyrazole-4-carboxamide No. C.87 SERENADE ® MAX N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- trifluoromethyl-1H-pyrazole-4-carboxamide No. C.88 SERENADE ® ASO N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- trifluoromethyl-1H-pyrazole-4-carboxamide No. C.89 SONATA ® N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- trifluoromethyl-1H-pyrazole-4-carboxamide No. C.90 BALLAD ® Plus N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- trifluoromethyl-1H-pyrazole-4-carboxamide No. C.91 RHAPSODY ® N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.92 SERENADE ® MAX N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.93 SERENADE ® ASO N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.94 SONATA ® N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.95 BALLAD ® Plus N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.96 RHAPSODY ® N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.97 SERENADE ® MAX N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.98 SERENADE ® ASO N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.99 SONATA ® N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.100 BALLAD ® Plus N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide No. C.101 RHAPSODY ® N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1-methyl-1H-pyrazole-4-carboxamide No. C.102 SERENADE ® MAX N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1-methyl-1H-pyrazole-4-carboxamide No. C.103 SERENADE ® ASO N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1-methyl-1H-pyrazole-4-carboxamide No. C.104 SONATA ® N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1-methyl-1H-pyrazole-4-carboxamide No. C.105 BALLAD ® Plus N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1-methyl-1H-pyrazole-4-carboxamide No. C.106 RHAPSODY ® N-(4′-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1-methyl-1H-pyrazole-4-carboxamide No. C.107 SERENADE ® MAX N-(4′-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1-methyl-1H-pyrazole-4-carboxamide No. C.108 SERENADE ® ASO N-(4′-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1-methyl-1H-pyrazole-4-carboxamide No. C.109 SONATA ® N-(4′-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1-methyl-1H-pyrazole-4-carboxamide No. C.110 BALLAD ® Plus N-(4′-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1-methyl-1H-pyrazole-4-carboxamide No. C.111 RHAPSODY ® N-(4′-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1H-pyrazole-4-carboxamide No. C.112 SERENADE ® MAX N-(4′-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1H-pyrazole-4-carboxamide No. C.113 SERENADE ® ASO N-(4′-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1H-pyrazole-4-carboxamide No. C.114 SONATA ® N-(4′-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1H-pyrazole-4-carboxamide No. C.115 BALLAD ® Plus N-(4′-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1H-pyrazole-4-carboxamide No. C.116 RHAPSODY ® isopyrazam No. C.117 SERENADE ® MAX isopyrazam No. C.118 SERENADE ® ASO isopyrazam No. C.119 SONATA ® isopyrazam No. C.120 BALLAD ® Plus isopyrazam

TABLE 5 Active compound combinations of a component 1) and a component 2), conprising a compound II selected from group D): Mixture Component 1) Component 2) No. D.1 RHAPSODY ® 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine No. D.2 SERENADE ® MAX 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine No. D.3 SERENADE ® ASO 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine No. D.4 SONATA ® 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine No. D.5 BALLAD ® Plus 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine No. D.6 RHAPSODY ® 3,4,5-trichloro-pyridine-2,6-di-carbonitrile No. D.7 SERENADE ® MAX 3,4,5-trichloro-pyridine-2,6-di-carbonitrile No. D.8 SERENADE ® ASO 3,4,5-trichloro-pyridine-2,6-di-carbonitrile No. D.9 SONATA ® 3,4,5-trichloro-pyridine-2,6-di-carbonitrile No. D.10 BALLAD ® Plus 3,4,5-trichloro-pyridine-2,6-di-carbonitrile No. D.11 RHAPSODY ® N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloro-nicotinamide No. D.12 SERENADE ® MAX N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloro-nicotinamide No. D.13 SERENADE ® ASO N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloro-nicotinamide No. D.14 SONATA ® N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloro-nicotinamide No. D.15 BALLAD ® Plus N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloro-nicotinamide No. D.16 RHAPSODY ® N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4- dichloro-nicotinamide No. D.17 SERENADE ® MAX N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4- dichloro-nicotinamide No. D.18 SERENADE ® ASO N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4- dichloro-nicotinamide No. D.19 SONATA ® N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4- dichloro-nicotinamide No. D.20 BALLAD ® Plus N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4- dichloro-nicotinamide No. D.21 RHAPSODY ® diflumetorim No. D.22 SERENADE ® MAX diflumetorim No. D.23 SERENADE ® ASO diflumetorim No. D.24 SONATA ® diflumetorim No. D.25 BALLAD ® Plus diflumetorim No. D.26 RHAPSODY ® nitrapyrin No. D.27 SERENADE ® MAX nitrapyrin No. D.28 SERENADE ® ASO nitrapyrin No. D.29 SONATA ® nitrapyrin No. D.30 BALLAD ® Plus nitrapyrin No. D.31 RHAPSODY ® dodemorph-acetate No. D.32 SERENADE ® MAX dodemorph-acetate No. D.33 SERENADE ® ASO dodemorph-acetate No. D.34 SONATA ® dodemorph-acetate No. D.35 BALLAD ® Plus dodemorph-acetate No. D.36 RHAPSODY ® fluoroimid No. D.37 SERENADE ® MAX fluoroimid No. D.38 SERENADE ® ASO fluoroimid No. D.39 SONATA ® fluoroimid No. D.40 BALLAD ® Plus fluoroimid No. D.41 RHAPSODY ® blasticidin-S No. D.42 SERENADE ® MAX blasticidin-S No. D.43 SERENADE ® ASO blasticidin-S No. D.44 SONATA ® blasticidin-S No. D.45 BALLAD ® Plus blasticidin-S No. D.46 RHAPSODY ® chinomethionat No. D.47 SERENADE ® MAX chinomethionat No. D.48 SERENADE ® ASO chinomethionat No. D.49 SONATA ® chinomethionat No. D.50 BALLAD ® Plus chinomethionat No. D.51 RHAPSODY ® debacarb No. D.52 SERENADE ® MAX debacarb No. D.53 SERENADE ® ASO debacarb No. D.54 SONATA ® debacarb No. D.55 BALLAD ® Plus debacarb No. D.56 RHAPSODY ® difenzoquat No. D.57 SERENADE ® MAX difenzoquat No. D.58 SERENADE ® ASO difenzoquat No. D.59 SONATA ® difenzoquat No. D.60 BALLAD ® Plus difenzoquat No. D.61 RHAPSODY ® difenzoquat-methylsulphat No. D.62 SERENADE ® MAX difenzoquat-methylsulphat No. D.63 SERENADE ® ASO difenzoquat-methylsulphat No. D.64 SONATA ® difenzoquat-methylsulphat No. D.65 BALLAD ® Plus difenzoquat-methylsulphat No. D.66 RHAPSODY ® oxolinic acid No. D.67 SERENADE ® MAX oxolinic acid No. D.68 SERENADE ® ASO oxolinic acid No. D.69 SONATA ® oxolinic acid No. D.70 BALLAD ® Plus oxolinic acid No. D.71 RHAPSODY ® piperalin No. D.72 SERENADE ® MAX piperalin No. D.73 SERENADE ® ASO piperalin No. D.74 SONATA ® piperalin No. D.75 BALLAD ® Plus piperalin No. D.76 RHAPSODY ® 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluoro- phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine No. D.77 SERENADE ® MAX 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluoro- phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine No. D.78 SERENADE ® ASO 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluoro- phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine No. D.79 SONATA ® 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluoro- phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine No. D.80 BALLAD ® Plus 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluoro- phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine No. D.81 RHAPSODY ® 6-(3,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.82 SERENADE ® MAX 6-(3,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.83 SERENADE ® ASO 6-(3,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.84 SONATA ® 6-(3,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.85 BALLAD ® Plus 6-(3,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.86 RHAPSODY ® 6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.87 SERENADE ® MAX 6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.88 SERENADE ® ASO 6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.89 SONATA ® 6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.90 BALLAD ® Plus 6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.91 RHAPSODY ® 5-methyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.92 SERENADE ® MAX 5-methyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.93 SERENADE ® ASO 5-methyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.94 SONATA ® 5-methyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.95 BALLAD ® Plus 5-methyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.96 RHAPSODY ® 5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.97 SERENADE ® MAX 5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.98 SERENADE ® ASO 5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.99 SONATA ® 5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.100 BALLAD ® Plus 5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.101 RHAPSODY ® 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-2,7- diamine No. D.102 SERENADE ® MAX 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-2,7- diamine No. D.103 SERENADE ® ASO 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-2,7- diamine No. D.104 SONATA ® 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-2,7- diamine No. D.105 BALLAD ® Plus 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-2,7- diamine No. D.106 RHAPSODY ® 6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl- amine No. D.107 SERENADE ® MAX 6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl- amine No. D.108 SERENADE ® ASO 6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl- amine No. D.109 SONATA ® 6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl- amine No. D.110 BALLAD ® Plus 6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl- amine No. D.111 RHAPSODY ® 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.112 SERENADE ® MAX 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.113 SERENADE ® ASO 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.114 SONATA ® 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.115 BALLAD ® Plus 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.116 RHAPSODY ® 5-ethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.117 SERENADE ® MAX 5-ethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.118 SERENADE ® ASO 5-ethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.119 SONATA ® 5-ethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.120 BALLAD ® Plus 5-ethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.121 RHAPSODY ® 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.122 SERENADE ® MAX 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.123 SERENADE ® ASO 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.124 SONATA ® 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.125 BALLAD ® Plus 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7- ylamine No. D.126 RHAPSODY ® 5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.127 SERENADE ® MAX 5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.128 SERENADE ® ASO 5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.129 SONATA ® 5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.130 BALLAD ® Plus 5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.131 RHAPSODY ® 6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.132 SERENADE ® MAX 6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.133 SERENADE ® ASO 6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.134 SONATA ® 6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.135 BALLAD ® Plus 6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5- a]pyrimidin-7-ylamine No. D.136 RHAPSODY ® 5-trifluoromethyl-6-(3,5,5-trimethylhexyl)- [1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine No. D.137 SERENADE ® MAX 5-trifluoromethyl-6-(3,5,5-trimethylhexyl)- [1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine No. D.138 SERENADE ® ASO 5-trifluoromethyl-6-(3,5,5-trimethylhexyl)- [1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine No. D.139 SONATA ® 5-trifluoromethyl-6-(3,5,5-trimethylhexyl)- [1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine No. D.140 BALLAD ® Plus 5-trifluoromethyl-6-(3,5,5-trimethylhexyl)- [1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine

TABLE 6 Active compound combinations of a component 1) and a component 2), conprising a compound II selected from group E): Mixture Component 1) Component 2) No. E.1 RHAPSODY ® methasulphocarb No. E.2 SERENADE ® MAX methasulphocarb No. E.3 SERENADE ® ASO methasulphocarb No. E.4 SONATA ® methasulphocarb No. E.5 BALLAD ® Plus methasulphocarb No. E.6 RHAPSODY ® propamocarb hydrochloride No. E.7 SERENADE ® MAX propamocarb hydrochloride No. E.8 SERENADE ® ASO propamocarb hydrochloride No. E.9 SONATA ® propamocarb hydrochloride No. E.10 BALLAD ® Plus propamocarb hydrochloride

TABLE 7 Active compound combinations of a component 1) and a component 2), conprising a compound II selected from group F): Mixture Component 1) Component 2) No. F.1 RHAPSODY ® metrafenone No. F.2 SERENADE ® MAX metrafenone No. F.3 SERENADE ® ASO metrafenone No. F.4 SONATA ® metrafenone No. F.5 BALLAD ® Plus metrafenone No. F.6 RHAPSODY ® dodine free base No. F.7 SERENADE ® MAX dodine free base No. F.8 SERENADE ® ASO dodine free base No. F.9 SONATA ® dodine free base No. F.10 BALLAD ® Plus dodine free base No. F.11 RHAPSODY ® guazatine-acetate No. F.12 SERENADE ® MAX guazatine-acetate No. F.13 SERENADE ® ASO guazatine-acetate No. F.14 SONATA ® guazatine-acetate No. F.15 BALLAD ® Plus guazatine-acetate No. F.16 RHAPSODY ® iminoctadine-triacetate No. F.17 SERENADE ® MAX iminoctadine-triacetate No. F.18 SERENADE ® ASO iminoctadine-triacetate No. F.19 SONATA ® iminoctadine-triacetate No. F.20 BALLAD ® Plus iminoctadine-triacetate No. F.21 RHAPSODY ® iminoctadine-tris(albesilate) No. F.22 SERENADE ® MAX iminoctadine-tris(albesilate) No. F.23 SERENADE ® ASO iminoctadine-tris(albesilate) No. F.24 SONATA ® iminoctadine-tris(albesilate) No. F.25 BALLAD ® Plus iminoctadine-tris(albesilate) No. F.26 RHAPSODY ® kasugamycin-hydrochlorid-hydrat No. F.27 SERENADE ® MAX kasugamycin-hydrochlorid-hydrat No. F.28 SERENADE ® ASO kasugamycin-hydrochlorid-hydrat No. F.29 SONATA ® kasugamycin-hydrochlorid-hydrat No. F.30 BALLAD ® Plus kasugamycin-hydrochlorid-hydrat No. F.31 RHAPSODY ® dichlorophen No. F.32 SERENADE ® MAX dichlorophen No. F.33 SERENADE ® ASO dichlorophen No. F.34 SONATA ® dichlorophen No. F.35 BALLAD ® Plus dichlorophen No. F.36 RHAPSODY ® pentachlorophenol No. F.37 SERENADE ® MAX pentachlorophenol No. F.38 SERENADE ® ASO pentachlorophenol No. F.39 SONATA ® pentachlorophenol No. F.40 BALLAD ® Plus pentachlorophenol No. F.41 RHAPSODY ® N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide No. F.42 SERENADE ® MAX N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide No. F.43 SERENADE ® ASO N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide No. F.44 SONATA ® N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide No. F.45 BALLAD ® Plus N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide No. F.46 RHAPSODY ® dicloran No. F.47 SERENADE ® MAX dicloran No. F.48 SERENADE ® ASO dicloran No. F.49 SONATA ® dicloran No. F.50 BALLAD ® Plus dicloran No. F.51 RHAPSODY ® nitrothal-isopropyl No. F.52 SERENADE ® MAX nitrothal-isopropyl No. F.53 SERENADE ® ASO nitrothal-isopropyl No. F.54 SONATA ® nitrothal-isopropyl No. F.55 BALLAD ® Plus nitrothal-isopropyl No. F.56 RHAPSODY ® tecnazen No. F.57 SERENADE ® MAX tecnazen No. F.58 SERENADE ® ASO tecnazen No. F.59 SONATA ® tecnazen No. F.60 BALLAD ® Plus tecnazen No. F.61 RHAPSODY ® biphenyl No. F.62 SERENADE ® MAX biphenyl No. F.63 SERENADE ® ASO biphenyl No. F.64 SONATA ® biphenyl No. F.65 BALLAD ® Plus biphenyl No. F.66 RHAPSODY ® bronopol No. F.67 SERENADE ® MAX bronopol No. F.68 SERENADE ® ASO bronopol No. F.69 SONATA ® bronopol No. F.70 BALLAD ® Plus bronopol No. F.71 RHAPSODY ® diphenylamine No. F.72 SERENADE ® MAX diphenylamine No. F.73 SERENADE ® ASO diphenylamine No. F.74 SONATA ® diphenylamine No. F.75 BALLAD ® Plus diphenylamine No. F.76 RHAPSODY ® mildiomycin No. F.77 SERENADE ® MAX mildiomycin No. F.78 SERENADE ® ASO mildiomycin No. F.79 SONATA ® mildiomycin No. F.80 BALLAD ® Plus mildiomycin No. F.81 RHAPSODY ® oxin-copper No. F.82 SERENADE ® MAX oxin-copper No. F.83 SERENADE ® ASO oxin-copper No. F.84 SONATA ® oxin-copper No. F.85 BALLAD ® Plus oxin-copper No. F.86 RHAPSODY ® prohexadione calcium No. F.87 SERENADE ® MAX prohexadione calcium No. F.88 SERENADE ® ASO prohexadione calcium No. F.89 SONATA ® prohexadione calcium No. F.90 BALLAD ® Plus prohexadione calcium No. F.91 RHAPSODY ® N-(cyclopropylmethoxyimino-(6-difluoromethoxy- 2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide No. F.92 SERENADE ® MAX N-(cyclopropylmethoxyimino-(6-difluoromethoxy- 2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide No. F.93 SERENADE ® ASO N-(cyclopropylmethoxyimino-(6-difluoromethoxy- 2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide No. F.94 SONATA ® N-(cyclopropylmethoxyimino-(6-difluoromethoxy- 2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide No. F.95 BALLAD ® Plus N-(cyclopropylmethoxyimino-(6-difluoromethoxy- 2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide No. F.96 RHAPSODY ® N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.97 SERENADE ® MAX N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.98 SERENADE ® ASO N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.99 SONATA ® N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.100 BALLAD ® Plus N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.101 RHAPSODY ® N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.102 SERENADE ® MAX N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.103 SERENADE ® ASO N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.104 SONATA ® N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.105 BALLAD ® Plus N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5- dimethyl-phenyl)-N-ethyl-N-methyl formamidine No. F.106 RHAPSODY ® N′-(2-methyl-5-trifluormethyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.107 SERENADE ® MAX N′-(2-methyl-5-trifluormethyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.108 SERENADE ® ASO N′-(2-methyl-5-trifluormethyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.109 SONATA ® N′-(2-methyl-5-trifluormethyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.110 BALLAD ® Plus N′-(2-methyl-5-trifluormethyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.111 RHAPSODY ® N′-(5-difluormethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.112 SERENADE ® MAX N′-(5-difluormethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.113 SERENADE ® ASO N′-(5-difluormethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.114 SONATA ® N′-(5-difluormethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine No. F.115 BALLAD ® Plus N′-(5-difluormethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine

The compositions comprising the components 1) and 2), or the simultaneous, that is joint or separate, use of a component 1) and a component 2), are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi in particular from the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). Some of them are systemically active and can be used in crop protection as foliar fungicides, as soil fungicides and as fungicides for seed dressing.

The compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; beet, for example sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.

Preferably, compounds I and compositions thereof are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.

The term “plant propagation material” is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be mentioned. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.

Preferably, treatment of plant propagation materials with compounds I and compositions thereof is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

The term “cultivated plants” is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.

The term “cultivated plants” is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. U.S. Pat. No. 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e.g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants capable to synthesize one or more insecticidal proteins are, for example, described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus (corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivars producing the Cry1Ac toxin), Bollgard® II (cotton cultivars producing Cry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Btl 1 (e.g. Agrisure®CB) and Btl 76 from Syngenta Seeds SAS, France, (corn cultivars producing the Cry1Ab toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1F toxin and PAT enzyme).

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

The term “cultivated plants” is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera® rape).

The term “cultivated plants” is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato).

The term “protein” as used herein is to be understood as an oligopeptide or polypeptide or molecule made up of polypeptides including expressly also pre-proteins, hybrid proteins, peptides, truncated or otherwise modified proteins including those derived from post-transcriptional modifications such as acylation (e.g. acetylation, the addition of an acetyl group, usually at the N-terminus of the protein), alkylation, the addition of an alkyl group (e.g. addition of ethyl or methyl, usually at lysine or arginine residues) or demethylation, amidation at C-terminus, biotinylation (acylation of conserved lysine residues with a biotin appendage), formylation, γ-carboxylation dependent on Vitamin K, glutamylation (covalent linkage of glutamic acid residues), glycosylation (addition of a glycosyl group to either asparagine, hydroxylysine, serine, or threonine, resulting in a glycoprotein), glycation (nonenzymatic attachment of sugars), glycylation (covalent linkage of one to more glycine residues), covalent attachment of a heme moiety, hydroxylation, iodination, isoprenylation (addition of an isoprenoid group such as farnesol and geranylgeraniol), lipoylation (attachment of a lipoate functionality) including prenylation, GPI anchor formation (e.g. myristoylation, farnesylation and geranylgeranylation), covalent attachment of nucleotides or derivatives thereof including ADP-ribosylation and flavin attachment, oxidation, pegylation, covalent attachment of phosphatidylinositol, phosphopantetheinylation (addition of a 4′-phosphopantetheinyl moiety from coenzyme A), phosphorylation (addition of a phosphate group, usually to serine, tyrosine, threonine or histidine), pyroglutamate formation, racemization of proline, tRNA-mediated addition of amino acids such as arginylation, sulfation (addition of a sulfate group to a tyrosine), selenoylation (co-translational incorporation of selenium in selenoproteins), ISGylation (covalent linkage to the ISG15 protein [Interferon-stimulated Gene 15]), SUMOylation (covalent linkage to the SUMO protein [Small Ubiquitin-related MOdifier]), ubiquitination (covalent linkage to the protein ubiquitin or poly-ubiquitin), citrullination or deimination (conversion of arginine to citrulline), deamidation (conversion of glutamine to glutamic acid or asparagine to aspartic acid), formation of disulfide bridges (covalent linkage of two cysteine amino acids) or proteolytic cleavage (cleavage of a protein at a peptide bond).

The plants or seed treated with the combinations comprising components 1) and 2) may by wildlife types, plants or seed obtained by breeding and transgenic plants as well as their seed.

They are especially suitable for controlling the following phytopathogenic fungi:

Alternaria atrans tenuissima Diaporthe phaseolorum var. caulivora

Alternaria brassicae Drechslera glycini

Alternaria spp. Epicoccum spp.

Ascochyta tritici Erwinia amylovora

Blumeria graminis Erysiphe graminis

Botrytis cinerea Frogeye sojina

Bremia lactucae Fusarium solani

Bremia lucinae Fusarium culmorum

Calonectria crotalariae Fusarium graminearum

Cercospora canescens Gaeumannomyces graminis

Cercospora kikuchii Leptosphaeria nodorum

Cercospora sojina Leptosphaerulina trifolii

Cercospora canescens Macrophomina phaseolina

Choanephora infundibulifera Microdochium nivale

Cladosporium herbarum Microsphaera diffusa

Cochliobolus sativus Mycoleptodiscus terrestris

Cochliobolus sativus Neocosmospora vasinfecta

Colletotrichum truncatum Pellicularia sasakii

Corynespora cassiicola Peronospora brassicae

Dactuliophora glycines Peronospora manshurica

Dematophora necatrix Peronospora brassicae

Diaporthe phaseolorum Peronospora pisi

Phakopsora pachyrhizi Pyrenophora convohuli

Phakopsora meibomiae Pyrenophora coppeyana

Phialophora gregata Pyrenophora cytisi

Phomopsis phaseoli Pyrenophora dactylidis

Phyllostica sojaecola Pyrenophora dictyoides

Physiological leaf spots Pyrenophora echinopis

Phythium ultimum Pyrenophora ephemera

Phytophthora megasperma Pyrenophora eryngicola

Phytophthora infestans Pyrenophora erythrospila

Phytopthora megasperma Pyrenophora euphorbiae

Plasmopara viticola Pyrenophora freticola

Podosphaera leucotricha Pyrenophora graminea

Podosphaera leucotricha Pyrenophora graminea

Pseudocercospora herpotrichoides Pyrenophora heraclei

Pseudomonas lachrymans Pyrenophora hordei

Pseudomonas syringae Pyrenophora horrida

Pseudoperonospora cubensis Pyrenophora hyperici

Pseudoperonospora humuli Pyrenophora japonica

Puccinia hordei Pyrenophora kugitangi

Puccinia recondita Pyrenophora lithophila

Puccinia striiformis Pyrenophora lolii

Puccinia triticina Pyrenophora macrospora

Pyrenochaeta glycines Pyrenophora metasequoiae

Pyrenophora allosuri Pyrenophora minuertiae hirsutae

Pyrenophora altermarina Pyrenophora moravica

Pyrenophora avenae Pyrenophora moroczkowskii

Pyrenophora bartramiae Pyrenophora muscorum

Pyrenophora bondarzevii Pyrenophora osmanthi

Pyrenophora bromi Pyrenophora phlei

Pyrenophora bryophila Pyrenophora pimpinellae

Pyrenophora buddleiae Pyrenophora pittospori

Pyrenophora bupleuri Pyrenophora polytricha

Pyrenophora calvertii Pyrenophora pontresinerisis

Pyrenophora calvescens var. moravica Pyrenophora pulsatillae

Pyrenophora carthanie Pyrenophora raetica

Pyrenophora centranthi Pyrenophora rayssiae

Pyrenophora cerastii Pyrenophora rugosa

Pyrenophora chengii Pyrenophora ryohicola

Pyrenophora chrysamthemi Pyrenophora saviczii

Pyrenophora schoeteri Rhizoctonia anomala

Pyrenophora scholevskii Rhizoctonia apocynacearum

Pyrenophora scirpi Rhizoctonia arachnion

Pyrenophora scirpicola Rhizoctonia asclerotica

Pyrenophora secalis Rhizoctonia batalicola

Pyrenophora semeniperda Rhizoctonia borealis

Pyrenophora semiusta Rhizoctonia callae

Pyrenophora seseli Rhizoctonia carorae

Pyrenophora seseli f. poterii Rhizoctonia cerealis

Pyrenophora subalpina Rhizoctonia choussii

Pyrenophora sudetica Rhizoctonia coniothecioides

Pyrenophora suhantarctica Rhizoctonia cundida

Pyrenophora syntrichiae Rhizoctonia dichoroma

Pyrenophora szaferiana Rhizoctonia dimorpha

Pyrenophora teres Rhizoctonia endophytica

Pyrenophora teres f. makulata Rhizoctonia endophytica vor. filicata

Pyrenophora teres subsp. graminea Rhizoctonia ferruginea

Pyrenophora tetrahenae Rhizoctonia floccosa

Pyrenophora tranzschelii Rhizoctonia fragariae

Pyrenophora trifulii Rhizoctonia fraxini

Pyrenophora triticil-repentis Rhizoctonia fuliginea

Pyrenophora ushuwaiensis Rhizoctonia fumigata

Pyrenophora villose Rhizoctonia globularis

Pyrenophora graminea Rhizoctonia goodyerae-repentis

Pyrenophora teres Rhizoctonia gossypii

Pyrenophora teres Rhizoctonia gossypii vor. anatolica

Pyrenophora teres Rhizoctonia gracilis

Pyrenophora tritici repentis Rhizoctonia griseo

Pyricularia oryzae Rhizoctonia hiemalis

Pythium aphanidermatum Rhizoctonia juniperi

Pythium debaryanum Rhizoctonia lamallifera

Pythium irregulare Rhizoctonia leguminicola

Pythium myriotylum Rhizoctonia lilacina

Pythium ultimum Rhizoctonia luoini

Ramularia collocygni Rhizoctonia macrosclerotia

Rhizoctonia aerea Rhizoctonia melongenae

Rhizoctonia alba Rhizoctonia microsclerotia

Rhizoctonia alpina Rhizoctonia monilioides

Rhizoctonia anaticula Rhizoctonia monteithiana

Rhizoctonia muneratii Tilletia aegopogonis

Rhizoctonia nandorii Tilletia ahamadiana

Rhizoctonia oryzae Tilletia airina

Rhizoctonia oryzae-sativae Tilletia ajrekari

Rhizoctonia pallida Tilletia alopecuri

Rhizoctonia pini-insignis Tilletia anthaxanthi

Rhizoctonia praticola Tilletia apludae

Rhizoctonia quercus Tilletia armdinellae

Rhizoctonia ramicola Tilletia asperifolia

Rhizoctonia robusta Tilletia asperitolioides

Rhizoctonia rubi Tilletia atacamensis

Rhizoctonia ruhiginosa Tilletia baldrati

Rhizoctonia sclerotica Tilletia bambusae

Rhizoctonia solani Tilletia banarasae

Rhizoctonia solani f. paroketea Tilletia bangalorensis

Rhizoctonia solani forma specialis Tilletia barclayana

Rhizoctonia solani var. cedri-deodorae Tilletia biharica

Rhizoctonia solani var. fuchsiae Tilletia boliviensis

Rhizoctonia solani var. hortensis Tilletia boutelouae

Rhizoctonia stahlii Tilletia brachypodii

Rhizoctonia subtilis var. nigra Tilletia brachypodii-ramosi

Rhizoctonia subtlilis Tilletia braomi-tectorum

Rhizoctonia tomato Tilletia brevifaciens

Rhizoctonia tuliparum Tilletia bromi

Rhizoctonia veae Tilletia bromina

Rhizoctonia versicolor Tilletia brunkii

Rhizoctonia cerealis Tilletia buchloeana

Rhynchosporium secalis Tilletia bulayi

Sclerotina rolfsii Tilletia caries

Sclerotinia rolfsii Tilletia cathcariae

Sclerotinia sclerotiorum Tilletia cerebrina

Septoria glycines Tilletia chloridicola

Septoria nodorum Tilletia contaoversa

Septoria tritici Tilletia contraversa var. prostrata

Sphaerotheca fuliginea Tilletia contraversa var. elyni

Stagonospora nodorum Tilletia corona

Stemphylium botryosum Tilletia cynasuri

Thielaviopsis basicola Tilletia damacarae

Tilletia aegilopis Tilletia deyeuxiae

Tilletia digitariicola Tilletia laguri

Tilletia durangensis Tilletia leptochlase

Tilletia earlei Tilletia lepturi

Tilletia echinochlave Tilletia macrotuberculata

Tilletia echinochloae Tilletia madeirensis

Tilletia echinosperma Tilletia maglagonii

Tilletia ehrhartae Tilletia makutensis

Tilletia eleusines Tilletia milti

Tilletia elymandrae Tilletia milti-vernalis

Tilletia elymicola Tilletia montana

Tilletia elyni Tilletia montemartinii

Tilletia elythrophori Tilletia nanifica

Tilletia eragrostidis Tilletia narasimhanii

Tilletia euphorbiae Tilletia narayanaoana

Tilletia fahrendorfii Tilletia narduri

Tilletia festinca-octoflorana Tilletia nigrifaciens

Tilletia foelida Tilletia obscura-reticulora

Tilletia foliicola Tilletia oklahomae

Tilletia fusca Tilletia okudoirae

Tilletia fusca var. bromi-tectorum Tilletia oplistneni-cristati

Tilletia fusca var. guyotiana Tilletia paae

Tilletia fusca var. paragonica Tilletia pachyderma

Tilletia georfischeri Tilletia pallida

Tilletia gigaspora Tilletia panici

Tilletia goloskokovii Tilletia panici. humilis

Tilletia haynaldiae Tilletia paonensis

Tilletia heterospora Tilletia paraloxa

Tilletia holci Tilletia paspali

Tilletia hordei var. spontanei Tilletia pennisetina

Tilletia horrida Tilletia peritidis

Tilletia hyalospora var. cuzcoensis Tilletia phalaridis

Tilletia hyparrheniae Tilletia polypoganis

Tilletia indica Tilletia prostrata

Tilletia iniermedia Tilletia pulcherrima var. brachiariae

Tilletia iovensis Tilletia redfieldiae

Tilletia ixophari Tilletia rhei

Tilletia koeleriae Tilletia rugispora

Tilletia kuznetzoviana Tilletia sabaudiae

Tilletia laevis Tilletia salzmanii

Tilletia savilei Ustilago agrostis-palustris

Tilletia scrobiculata Ustilago airear-caespitosae

Tilletia setariae Ustilago alismatis

Tilletia setariae-palmiflorarae Ustilago almadina

Tilletia setariicola Ustilago alopecurivara

Tilletia sphaerococca Ustilago alsineae

Tilletia sphenopie Ustilago altilis

Tilletia sphenopodis Ustilago amadelpha var. glabriuscula

Tilletia sterilis Ustilago amphilophidis

Tilletia taiana Ustilago amplexa

Tilletia texana Ustilago amthoxanthi

Tilletia themedae-anatherae Ustilago andropogonis-tectorum

Tilletia themedicola Ustilago aneilemae

Tilletia toguateei Ustilago anhweiona

Tilletia trachypogonis Ustilago anomala var. avicularis

Tilletia transiliensis Ustilago anomala var. carnea

Tilletia transvaalensis Ustilago anomala var. cordai

Tilletia tritici f. monococci Ustilago anomala var. microspora

Tilletia tritici var. controversa Ustilago anomala var. muricata

Tilletia tritici var. nanifica Ustilago anomala var. tovarae

Tilletia tritici var. laevis Ustilago apscheronica

Tilletia tritici-repentis Ustilago arabidia.alpinae

Tilletia triticoides Ustilago arandinellae-hirtae

Tilletia tuberculare Ustilago arctica

Tilletia vertiveriae Ustilago argentina

Tilletia viermotii Ustilago aristidarius

Tilletia vittara Ustilago arotragostis

Tilletia vittara var. burmahnii Ustilago asparagi-pygmaei

Tilletia walkeri Ustilago asprellae

Tilletia youngii Ustilago avanae subsp. alba

Tilletia zundelii Ustilago avenae

Typhula incarnata Ustilago avenae

Uromyces appendiculatus Ustilago avenae f. sp. perennars

Ustilago aaeluropodis Ustilago avenariae-bryophyllae

Ustilago abstrusa Ustilago avicularis

Ustilago aegilopsidis Ustilago bahuichivoensis

Ustilago affinis var. hilariae Ustilago barbari

Ustilago agrestis Ustilago beckeropsis

Ustilago agropyrina Ustilago belgiana

Ustilago bethelii Ustilago clelandii

Ustilago bicolor Ustilago clintoniana

Ustilago bistortarum ustiloginea Ustilago coloradensis

Ustilago bistortarum var. pustulata Ustilago commelinae

Ustilago boreatis Ustilago compacta

Ustilago bothriochloae Ustilago concelata

Ustilago bothriochloae-intermediae Ustilago condigna

Ustilago bouriqueti Ustilago consimilis

Ustilago braziliensis Ustilago constantineanui

Ustilago brisae Ustilago controversa

Ustilago bromi-arvensis Ustilago conventere-sexualis

Ustilago bromi-erecti Ustilago cordai

Ustilago bromi-mallis Ustilago corlarderiae var. araucana

Ustilago bromina Ustilago coronariaw

Ustilago bromivora f. brachypodii Ustilago coronata

Ustilago bromivora var. microspora Ustilago courtoisii

Ustilago bullata f. brachypodii-distachyi Ustilago crus-galli var. minor

Ustilago bullata var. bonariesis Ustilago cryptica

Ustilago bullata var. macrospora Ustilago curta

Ustilago bungeana Ustilago custanaica

Ustilago calanagrostidis Ustilago cynodontis

Ustilago calanagrostidis var. scrobiculata Ustilago cynodontis

Ustilago calanagrostidis var. typica Ustilago cyperi-lucidi

Ustilago cardamines Ustilago davisii

Ustilago cariciphila Ustilago deccanii

Ustilago caricis-wallichianae Ustilago decipiens

Ustilago carnea Ustilago deformitis

Ustilago catherimae Ustilago dehiscens

Ustilago caulicola Ustilago delicata

Ustilago cenrtodomis Ustilago deyeuxiae

Ustilago ceparum Ustilago dianthorum

Ustilago cephalariae Ustilago distichlidis

Ustilago chacoensis Ustilago dubiosa

Ustilago chloridii Ustilago dumosa

Ustilago chloridionis Ustilago earlei

Ustilago chrysopoganis Ustilago echinochloae

Ustilago chubulensis Ustilago ehrhartana

Ustilago cichorii Ustilago eleocharidis

Ustilago cilmodis Ustilago eleusines

Ustilago elymicola Ustilago hilariicola

Ustilago elytrigiae Ustilago hilubii

Ustilago enneapogonis Ustilago himalensis

Ustilago epicampida Ustilago histortarum var. marginalis

Ustilago eragrostidis-japanicana Ustilago hitchcockiana

Ustilago eriocauli Ustilago holci-avanacei

Ustilago eriochloae Ustilago hordei

Ustilago euphorbiae Ustilago hordei f. sp. avenae

Ustilago fagopyri Ustilago hsuii

Ustilago festucae Ustilago hyalino-bipolaris

Ustilago festucorum Ustilago hydropiperis

Ustilago filamenticola Ustilago hyparrheniae

Ustilago fingerhuthiae Ustilago hypodyies f. congoensis

Ustilago flectens Ustilago hypodytes f. sporaboli

Ustilago flonersii Ustilago hypodytes var. agrestis

Ustilago foliorum Ustilago idonea

Ustilago formosana Ustilago imperatue

Ustilago fueguina Ustilago induia

Ustilago gageae Ustilago inouyei

Ustilago garcesi Ustilago intercedens

Ustilago gardneri Ustilago iranica

Ustilago gausenii Ustilago isachnes

Ustilago gayazana Ustilago ischaemi-akoensis

Ustilago gigantispora Ustilago ischaemi-anthephoroides

Ustilago glyceriae Ustilago ixiolirii

Ustilago gregaria Ustilago ixophori

Ustilago grossheimii Ustilago jacksonii

Ustilago gunnerae Ustilago jacksonii var. vintonesis

Ustilago haesendocki var. chloraphorae Ustilago jaczevskyana

Ustilago haesendocki var. vargasii Ustilago jaczevskyana van. typica

Ustilago halophiloides Ustilago jaczevskyana var. sibirica

Ustilago haynalodiae Ustilago jagdishwari

Ustilago heleochloae Ustilago jamalainentii

Ustilago helictotrichi Ustilago jehudana

Ustilago herteri var. Bicolor Ustilago johnstonii

Ustilago herteri var. vargasii Ustilago kairamoi

Ustilago hierochloae-adoratae Ustilago kasuchstemica

Ustilago hieronymi var. insularis Ustilago kenjiana

Ustilago hieronymi var. minor Ustilago kweichowensis

Ustilago kylingae Ustilago mrucata

Ustilago lacjrymae-jobi Ustilago muda

Ustilago lepyrodiclidis Ustilago muehlenbergiae var. lucumanensis

Ustilago lidii Ustilago muscaribotryoidis

Ustilago liebenbergii Ustilago nagarnyi

Ustilago linderi Ustilago nannfeldtii

Ustilago linearis Ustilago nauda var. hordei

Ustilago lirove Ustilago nelsoniana

Ustilago loliicola Ustilago nepalensis

Ustilago longiflora Ustilago neyraudiae

Ustilago longiseti Ustilago nigra

Ustilago longissima var. dubiosa Ustilago nivalis

Ustilago longissima var. paludificans Ustilago nuda

Ustilago longissima var. typica Ustilago nuda

Ustilago lupini Ustilago nuda var. tritici

Ustilago lychnidis-dioicae Ustilago nyassae

Ustilago lycoperdiformis Ustilago okudairae

Ustilago lyginiae Ustilago olida

Ustilago machili Ustilago olivacea var. macrospora

Ustilago machringiae Ustilago onopordi

Ustilago magalaspora Ustilago onumae

Ustilago magellanica Ustilago opiziicola

Ustilago mariscana Ustilago oplismeni

Ustilago maydis Ustilago orientalis

Ustilago melicae Ustilago otophora

Ustilago merxmuellerana Ustilago ovariicola

Ustilago mesatlantica Ustilago overcemii

Ustilago michnoana Ustilago pamirica

Ustilago microspora Ustilago panici-geminati

Ustilago microspora var. paspalicola Ustilago panjabensis

Ustilago microstegii Ustilago pappophori

Ustilago microthelis Ustilago pappophori var. magdalensis

Ustilago milli Ustilago parasnothii

Ustilago mobtagnei var. minor Ustilago parodii

Ustilago modesta Ustilago parvula

Ustilago moenchiae-manticae Ustilago paspalidiicola

Ustilago monermae Ustilago patagonica

Ustilago morinae Ustilago penniseti var. verruculosa

Ustilago morobiana Ustilago perrara

Ustilago persicariae Ustilago scitaminea

Ustilago petrakii Ustilago scitaminea var. sacchar-officinorum

Ustilago phalaridis Ustilago scleranthi

Ustilago phlei Ustilago scrobiculata

Ustilago phlei-protensis Ustilago scutulata

Ustilago phragmites Ustilago secalis var. elymi

Ustilago picacea Ustilago seitaminea var. sacchari-barberi

Ustilago pimprina Ustilago semenoviana

Ustilago piperi (var.) rosulata Ustilago serena

Ustilago poae Ustilago serpens

Ustilago poae-bulbosae Ustilago sesleriae

Ustilago poae-nemoralis Ustilago setariae-mambassanae

Ustilago polygoni-alati Ustilago shastensis

Ustilago polygoni-alpini Ustilago shimadae

Ustilago polygoni-punctari Ustilago silenes-inflatae

Ustilago polygoni-serrulati Ustilago silenes-nutantis

Ustilago polytocae Ustilago sinkiangensis

Ustilago polytocae-harbatas Ustilago sitanil

Ustilago pospelovii Ustilago sleuneri

Ustilago prostrata Ustilago sonoriana

Ustilago pseudohieronymi Ustilago sorghi-stipoidei

Ustilago puehlaensis Ustilago spadicea

Ustilago puellaris Ustilago sparoboli-indici

Ustilago pulvertulensa Ustilago sparti

Ustilago raciborskiana Ustilago speculariae

Ustilago radians Ustilago spegazzinii

Ustilago ravida Ustilago spegazzinii var. agrestis

Ustilago rechingeri Ustilago spermophora var. orientalis

Ustilago reticulara Ustilago spermophoroides

Ustilago reticulispora Ustilago spinulosa

Ustilago rhei Ustilago sporoboli-trenuli

Ustilago rhynchelytri Ustilago stellariae

Ustilago ruandenis Ustilago sterilis

Ustilago ruberculata Ustilago stewartli

Ustilago sabouriana Ustilago stipae

Ustilago salviae Ustilago striaeformis f. phlei

Ustilago sanctae-catharinae Ustilago striaeformis f. poa . . .

Ustilago scaura Ustilago striaeformis f. poae-pratensis

Ustilago scillae Ustilago striiformis f. hierochloes-odoratae

Ustilago striiformis var. agrostidis Ustilago tucumariensis

Ustilago striiformis var. dactylidis Ustilago tumeformis

Ustilago striiformis var. holci Ustilago turcomanica

Ustilago striiformis var. phlei Ustilago turcomanica var. prostrata

Ustilago striiformis var. poae Ustilago turcomanica var. typica

Ustilago sumnevicziana Ustilago ugamica

Ustilago superha Ustilago ugandensis var. macrospora

Ustilago sydowiana Ustilago underwoodii

Ustilago symbiotica Ustilago urginede

Ustilago taenia Ustilago urochloana

Ustilago taiana Ustilago ustilaginea

Ustilago tanakue Ustilago ustriculosa var. cordai

Ustilago tenuispora Ustilago ustriculosa var. reticulata

Ustilago thaxteri Ustilago valentula

Ustilago tinontiae Ustilago vavilori

Ustilago togata Ustilago verecunda

Ustilago tournenxii Ustilago verruculosa

Ustilago tovarae Ustilago versatilis

Ustilago trachophora var. pacifica Ustilago vetiveriae

Ustilago trachyniae Ustilago violaceo-irregularis

Ustilago trachypogonis Ustilago violaceu var. stellariae

Ustilago tragana Ustilago violaceuverrucosa

Ustilago tragi Ustilago williamsii

Ustilago tragica Ustilago wynaadensis

Ustilago tragi-racemosi Ustilago zambettakisii

Ustilago trichoneurana Ustilago zernae

Ustilago trichophora var. crus-galli Venturia inaequalis

Ustilago trichophora var. panici-frumentacei Xanthomonas campestris

Ustilago triseti Xanthomonas oryzae

Ustilago tritici forma specialis

The compositions comprising the components 1) and 2) are particularly suitable for controlling phytopathogenic fungi in barley (e.g. Pyrenophora teres, Rhynchosporium secalis, Puccinia hordei, Puccinia striiformis, Blumeria graminis, Ramularia collo-cygni/Physiological leaf spots, Microdochium nivale, Typhula incarnata, Pseudocercosporella herpotrichoides, Fusarium culmorum, Rhizoctonia cerealis, Gaeumannomyces graminis) and soybeans (e.g. Phakopsora pachyrhizi, Microsphaera diffusa, Septoria glycines, Cercospora sojina, Cercospora kikuchii, Corynespora cassiicola, Colletotrichum truncatum, Peronospora manshurica, Alternaria spp., Phomopsis phaseoli, Diaporthe phaseolorum, Phialophora gregata, Fusarium solani, Sclerotinia sclerotiorum, Sclerotinia rolfsii, Phytopthora megasperma, Rhizoctonia solani, Dematophora necatrix, Macrophomina phaseolina).

The inventive compositions are particularly suitable for controlling phytopathogenic fungi in soybeans, vegetables and fruit crops.

The compositions according to the invention are furthermore suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In the protection of wood, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., additionally in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae.

Application of the inventive compositions to useful plants may also lead to an increase in the crop yield.

The components 1) and 2) can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.

When preparing the compositions, it is preferred to employ the commercially available formulations of components 1) and 2), to which further compounds active against harmful fungi or other pests, such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers may be added.

Usually, compositions comprising component 1) and 2), wherein component 2) consists of only one active ingredient (II), are employed. However, in certain cases compositions wherein component 2) consists of two or, if appropriate, more active components may be advantageous.

Suitable further active components in the above sense are in particular the active compounds II mentioned at the outset, and in particular the preferred active compounds II mentioned above.

Components 1) and 2) are usually employed in a weight ratio of from 100:1 to 1:100, preferably from 30:1 to 1:30, in particular from 15:1 to 1:15.

The further active components are, if desired, added in a ratio of from 20:1 to 1:20 to component 1).

Depending on the particular components and the desired effect, the application rates for component 1) are generally from 1 l to 100 l broth containing the strain per hectare, preferably from 1 l to 50 l/ha, in particular from 1 to 20 l/ha.

Correspondingly, the application rates for component 2) are generally from 1 to 2000 g/ha, preferably from 10 to 1500 g/ha, in particular from 40 to 1000 g/ha.

The method for controlling harmful fungi is carried out by the separate or joint application of a component 1) and a component 2), or a composition comprising components 1) and 2), by spraying or dusting the seeds, the plants or the soils before or after sowing of the plants or before or after emergence of the plants.

The compositions according to the invention, or the single components separately, can be converted into customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the mixture according to the invention.

The formulations are prepared in a known manner, for example by extending the single components with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries suitable for this purpose are essentially:

-   -   water, aromatic solvents (for example Solvesso® products,         xylene), paraffins (for example mineral oil fractions), alcohols         (for example methanol, butanol, pentanol, benzyl alcohol),         ketones (for example cyclohexanone, gamma-butyrolactone),         pyrrolidones (N-methylpyrrolidone, N-octylpyrrolidone), acetates         (glycol diacetate), glycols, fatty acid dimethylamides, fatty         acids and fatty acid esters. In principle, solvent mixtures may         also be used.     -   carriers such as ground natural minerals (for example kaolins,         clays, talc, chalk) and ground synthetic minerals (for example         highly disperse silica, silicates); emulsifiers such as         nonionogenic and anionic emulsifiers (for example         polyoxyethylene fatty alcohol ethers, alkylsulfonates and         arylsulfonates) and dispersants such as lignosulfite waste         liquors and methylcellulose.

Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.

Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In order to achieve good dispersion and adhesion of compositions within the present invention, it may be advantageous to formulate the whole broth culture, supernatant and/or metabolite with components that aid dispersion and adhesion.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the components.

The active compounds (II) are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The following are examples of formulations: 1. Products for dilution with water

A) Water-Soluble Concentrates (SL)

10 parts by weight of a composition according to the invention are dissolved in 90 parts by weight of water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. Dilution with water results in a formulation having a content of 10% by weight of components 1) and 2) is obtained.

B) Dispersible Concentrates (DC)

20 parts by weight of a composition according to the invention are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion having a content of 0% by weight of components 1) and 2).

C) Emulsifiable Concentrates (EC)

15 parts by weight of a composition according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has a content of 15% by weight of components 1) and 2).

D) Emulsions (EW, EO)

25 parts by weight of a composition according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This composition is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has a content of 25% by weight of components 1) and 2).

E) Suspensions (SC, OD)

In an agitated ball mill, 20 parts by weight of a composition according to the invention are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine suspension. Dilution with water gives a stable suspension having a content of 20% by weight of components 1) and 2).

F) Water-dispersible granules and water-soluble granules (WG, SG)

50 parts by weight of a composition according to the invention are ground finely with addition of 50 parts by weight of dispersants and wetting agents and prepared as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution having a content of 50% by weight of components 1) and 2).

G) Water-Dispersible Powders and Water-Soluble Powders (WP, SP)

75 parts by weight of a composition according to the invention are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution having a content of 75% by weight of components 1) and 2).

2. Products to be applied undiluted

H) Dustable powders (DP)

5 parts by weight of a composition according to the invention are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having a content of 5% by weight of components 1) and 2).

J) Granules (GR, FG, GG, MG)

0.5 part by weight of a composition according to the invention is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted having a content of 0.5% of weight of components 1) and 2).

K) ULV solutions (UL)

10 parts by weight of a composition according to the invention are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted having a compound content of 10% by weight of components 1) and 2).

Components 1) and 2) can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of components 1) and 2) according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The concentrations of the components in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 100%, preferably from 0.01 to 100%.

Components 1) and 2) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply components 1) and 2) without additives.

Oils of various types, wetting agents or adjuvants may be added to the component 1) or 2), even, if appropriate, not until immediately prior to use (tank mix). These agents are typically admixed with component 1) or 2) according to the invention in a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.

Suitable adjuvants in this sense are in particular: organically modified polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO/PO block polymers, for example Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates, for example Lutensol XP 80®; and sodium dioctylsulfosuccinate, for example Leophen RA®.

Components 1) and 2) or the composition comprising components 1) and 2), or the corresponding formulations, are applied by treating the harmful fungi, the plants, seeds, soils, areas, materials or spaces to be kept free from them with a fungicidally effective amount of the composition or, in the case of separate application, of the components 1) and 2) separately. Application can be before or after the infection by harmful fungi.

The fungicidal action of components 1) and 2) and of the compositions according to the invention was demonstrated by the tests below.

Components 1) and 2), separately or jointly, were prepared as a stock solution comprising 25 mg of active compound which was made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols) in a ratio by volume of solvent/emulsifier of 99:1. The mixture was then made up to 100 ml with water. This stock solution was diluted with the solvent/emulsifier/water mixture described to give the concentration of active compound stated below.

The visually determined percentages of infected leaf areas were converted into efficacies in % of the untreated control:

The efficacy (E) is calculated as follows using Abbot's formula:

E=(1−α/β)−100

α corresponds to the fungicidal infection of the treated plants in % and

β corresponds to the fungicidal infection of the untreated (control) plants in %

An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.

The expected efficacies of active compound combinations were determined using Colby's formula (Colby, S. R. “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies.

Colby's formula: E=x+y−X∘y/100

-   E expected efficacy, expressed in % of the untreated control, when     using the mixture of the active compounds A and B at the     concentrations a and b -   x efficacy, expressed in % of the untreated control, when using the     active compound A at the concentration a -   y efficacy, expressed in % of the untreated control, when using the     active compound B at the concentration b 

1. A fungicidal composition for controlling phytopathogenic harmful fungi, comprising 1) a fungicidal strain (I) selected from a) the Bacillus substilis subtilis strain with NRRL Accession No. B-21661, and b) the Bacillus pumilus strain with NRRL Accession No. B-30087, or a mutant of these strains having all the identifying characteristics of the respective strain, and 2) at least one chemical compound (II), wherein chemical compound (II) is a carbamate; in a synergistically effective amount.
 2. The fungicidal composition according to claim 1, comprising as component 1) a commercially available formulation of strain a) or b).
 3. The fungicidal composition according to claim 1 wherein chemical compound (II) is propamocarb propamocarb hydrochloride, or methasulphocarb.
 4. The fungicidal composition according to claim 3 wherein chemical compound (II) is propamocarb hydrochloride.
 5. The fungicidal composition according to claim 1 wherein component 1) is the Bacillus subtilis strain with NRRL Accession No. B-21661 or a mutant thereof having all the identifying characteristics of the strain.
 6. The fungicidal composition according to claim 1, comprising an additional active compound V, selected from the groups G) to M): G) azoles selected from the group consisting of bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imiben-conazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole and hymexazole; H) strobilurins selected from the group consisting of azoxystrobin, dimoxy-strobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)-carbamate and methyl 2-(ortho-(2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate; J) carboxamides selected from the group consisting of carboxin, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxy-phenyl)ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-ethanesulfonyl-amino-3-methylbutyramide, methyl 3-(4-chlorophenyl)-3-(2-isopropoxy-carbonylamino-3-methylbutyrylamino)propionate, N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methyl-thiazole-5-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoro-methyl-1-methylpyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide and N-(2-cyanophenyl)-3,4-dichloro-isothiazole-5-carboxamide; K) heterocyclic compounds selected from the group consisting of fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen and N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide; L) carbamates selected from the group consisting of mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flubenthiavalicarb, 4-fluorophenyl N-(1-(1-(4-cyanophenyl)ethanesulfonyl)but-2-yl)carbamate, methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methyl-butyrylamino)propanoate and carbamate oxime ethers of the formula VI

in which Z is N or CH; M) other fungicides selected from the group consisting of guanidine, dodine, iminoctadine, guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobuton, sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane, organometallic compounds: fentin salts, organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl, organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid, inorganic active compounds: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, others: cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl and spiroxamine.
 7. The fungicidal composition according to claim 1, comprising the components 1) and 2) in a weight ratio of from 100:1 to 1:100.
 8. A fungicidal agent, comprising at least one liquid or solid carrier and a fungicidal composition according to claim
 1. 9. A method for controlling harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil, seed, areas, materials or spaces are/is treated with an effective amount of a a fungicidal composition according to claim
 1. 10. The method according to claim 9, wherein components 1) and 2) are applied simultaneously, that is jointly or separately, or in succession.
 11. Seed, comprising a fungicidal composition according to claim
 1. 12-13. (canceled)
 14. The method of claim 9, wherein the components 1) and 2) are present in a weight ratio of from 100:1 to 1:100.
 15. The method of claim 9, wherein the fungicidal composition further comprises at least one liquid or solid carrier.
 16. A method for controlling harmful fungi, wherein a transgenic plant or the seed thereof is treated with a fungicidal agent suitable for controlling harmful fungi comprising a fungicidal composition according to claim
 1. 17. The method of claim 16, wherein components 1) and 2) are applied simultaneously, that is jointly or separately, or in succession.
 18. The method of claim 16, wherein the components 1) and 2) are present in a weight ratio of from 100:1 to 1:100.
 19. The method of claim 16, wherein the fungicidal composition further comprises at least one liquid or solid carrier. 